2-[4-(2-Oxo-2-trimethylsilanyl-ethyl)-phenyl]-1-trimethylsilanyl-ethanone | 833460-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-(2-Oxo-2-trimethylsilanyl-ethyl)-phenyl]-1-trimethylsilanyl-ethanone
• 英文别名: Silane, [1,4-phenylenebis(1-oxo-2,1-ethanediyl)]bis[trimethyl-；2-[4-(2-oxo-2-trimethylsilylethyl)phenyl]-1-trimethylsilylethanone
• CAS: 833460-63-2
• 化学式: C₁₆H₂₆O₂Si₂
• 分子量: 306.552
• InChiKey: BTOXRZADCPQWEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₂₂H₄₂O₂Si₄ 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 2-[4-(2-Oxo-2-trimethylsilanyl-ethyl)-phenyl]-1-trimethylsilanyl-ethanone
  参考文献：
  名称：

  1,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene: Regioselective ring opening of its α,β-epoxybis(silane) with some nucleophiles

  摘要：

  The Peterson olefination reaction of terephthalaldehyde with tris(trimethylsilyl) methyllithium, (Me3Si)(3)-CLi, in Et2O gives disubstituted vinylbis(silane) 1 which reacts with MCPBA in CH2Cl2 at r.t. to afford mixture of mono and disubstituted epoxybis(silanes) 3 and 2. Vinylbis(silane) 1 can be completely converted into epoxybis(silane) 2 with an excess amount of MCPBA. The compound 2 was reacted with various reagents such as HX (X = Cl, Br), H2SO4, LiAlH4 and MeLi/CuI and give the related products. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.01.030

文献信息

• Evaluation of C-trialkylsilyl enol and thioenol ethers as intermediates in the synthesis of acylsilanes
  作者：Catherine Hammaecher、Imad Ouzzane、Charles Portella、Jean-Philippe Bouillon

  DOI：10.1016/j.tet.2004.10.082

  日期：2005.1

  C-silyl enol ethers or thioenol ethers have been prepared by a Peterson reaction, as intermediates for acylsilane synthesis. Bis(trialkylsilyl)(methoxy)- or -(methylsulfanyl)methanes bearing identical or different trialkylsilyl groups were used as starting materials in order to assess the selectivity of the Peterson elimination step. A good selectivity was observed only with ethers bearing the TMS

  通过Peterson反应已经制备了C-甲硅烷基烯醇醚或硫烯醇醚，作为酰基硅烷合成的中间体。为了评估彼得森消除步骤的选择性，将带有相同或不同三烷基甲硅烷基的双（三烷基甲硅烷基）（甲氧基）-或-（甲基硫烷基）甲烷用作起始原料。仅用带有TMS和TBDMS基团的醚观察到良好的选择性。然而，由于难以以正确的产率获得这些试剂，因此没有实际的兴趣来使用这些试剂。事实证明，双（三甲基甲硅烷基）（甲基硫烷基）甲烷是制备C-甲硅烷基硫烯醇醚的良好试剂，C-甲硅烷基硫烯醇醚在传统的酸性条件下可以水解，从而以合理的总收率得到酰基硅烷。该方便的过程扩展到双（酰基硅烷）的合成。
• 1,4-bis[2,2-bis(trimethylsilyl)ethenyl]benzene: Regioselective ring opening of its α,β-epoxybis(silane) with some nucleophiles
  作者：Kazem D. Safa、Khatereh Ghorbanpour、Akbar Hassanpour、Shahin Tofangdarzadeh

  DOI：10.1016/j.jorganchem.2009.01.030

  日期：2009.5

  The Peterson olefination reaction of terephthalaldehyde with tris(trimethylsilyl) methyllithium, (Me3Si)(3)-CLi, in Et2O gives disubstituted vinylbis(silane) 1 which reacts with MCPBA in CH2Cl2 at r.t. to afford mixture of mono and disubstituted epoxybis(silanes) 3 and 2. Vinylbis(silane) 1 can be completely converted into epoxybis(silane) 2 with an excess amount of MCPBA. The compound 2 was reacted with various reagents such as HX (X = Cl, Br), H2SO4, LiAlH4 and MeLi/CuI and give the related products. (C) 2009 Elsevier B.V. All rights reserved.